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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Nitric Oxide Signaling Pathway01:28

Nitric Oxide Signaling Pathway

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Nitric oxide (NO), an inorganic gas, acts as a potent second messenger in most animal and plant tissues. NO diffuses out of the cells that produce it and enters the neighboring cells to generate a downstream response. NO synthase (NOS) catalyzes NO production by the deamination of the amino acid arginine. There are three isoforms of NOS. Endothelial cells have endothelial NOS (eNOS), nerve and muscle cells have neuronal NOS (nNOS), and macrophages produce inducible NOS (iNOS) upon exposure...
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.5K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.5K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

4.0K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Amines: Introduction01:07

Amines: Introduction

4.7K
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Updated: Sep 5, 2025

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
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Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

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Polymeric Amines Induce Nitric Oxide Release from S-Nitrosothiols.

Zijie Luo1, Gervase Ng1,2, Yingzhu Zhou1

  • 1School of Chemical Engineering and Australian Centre for Nanomedicine (ACN), The University of New South Wales (UNSW Sydney), Sydney, NSW, 2052, Australia.

Small (Weinheim an Der Bergstrasse, Germany)
|July 5, 2022
PubMed
Summary

Researchers discovered polymeric amines, like polyethyleneimine (PEI), can generate nitric oxide (NO) from S-nitrosothiols (RSNOs) under physiological conditions. This finding simplifies NO delivery for biomedical applications, offering new biomaterial development opportunities.

Keywords:
S-nitrosoglutathionesS-nitrosothiolsnitric oxidepolymers

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En Face Detection of Nitric Oxide and Superoxide in Endothelial Layer of Intact Arteries
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Area of Science:

  • Biomaterials Science
  • Polymer Chemistry
  • Chemical Biology

Background:

  • Nanomaterials enable nitric oxide (NO) generation for biomedical uses, but synthesis is complex.
  • Developing simpler methods for controlled NO release is crucial for advanced biomaterials.

Purpose of the Study:

  • To identify novel materials capable of inducing NO generation from S-nitrosothiols (RSNOs) under physiological conditions.
  • To elucidate the mechanism of NO generation by polymeric amines.
  • To demonstrate the utility of these NO-releasing polymers in functional biomaterials.

Main Methods:

  • Screening of polymeric amines (polyethyleneimine (PEI), poly-L-lysine, poly(allylamine hydrochloride)) for NO generation from RSNOs.
  • Investigating the mechanism of NO release via nucleophilic reactions.
  • Incorporating PEI into poly(vinyl alcohol) (PVA) hydrogels.
  • Evaluating the antibacterial efficacy of PVA/PEI hydrogels against Pseudomonas aeruginosa biofilms.

Main Results:

  • Polymeric amines were identified as effective catalysts for NO generation from RSNOs at physiological conditions.
  • NO generation rate can be controlled by polymer type, molecular weight, and RSNO concentration.
  • The mechanism involves a nucleophilic reaction between polymer primary amines and RSNO groups.
  • PEI-integrated PVA hydrogels demonstrated significant Pseudomonas aeruginosa biofilm inhibition (≈4 log reduction in 6h).

Conclusions:

  • Polymeric amines offer a facile route for NO generation from RSNOs, overcoming limitations of nanomaterial-based approaches.
  • This discovery enables the development of versatile NO-releasing biomaterials for diverse therapeutic applications.
  • Potential applications include antibacterial, antiviral, anticancer, antithrombotic, and wound healing strategies.